Longtime reader, very rare commenter but I think you generally give excellent advice so I’m giving it a shot. I’ll try to keep this relatively brief – I’m having an existential problem surrounding life milestones, etc. I’m 25 and have generally been pretty successful in my life – I’ve been academically successful, I have a law degree and a good job, and I have a really good group of friends, most of whom have been in my life for many years.

What I haven’t had is a whole lot of romantic relationships. This is generally fine with me. I really value my personal space and don’t generally crave the kind of constant companionship that comes with serious relationships. I’ve dumped people for “liking me too much” (ie, coming on too strong, wanting a kind of closeness I wasn’t comfortable with, etc). I’ve had one relationship that I would classify as “semi-serious” with a much older man that I met several years ago (we are still close and sometimes physically involved but not currently “in a relationship”). This relationship used to cause me a lot of emotional pain but I’m at peace with it now and don’t consider it a source of stress in my life. Additionally, I am kind of wary of men (I haven’t been raped or abused, fortunately, but have had the same experiences as a lot of women – sexual harassment, etc, lots of friends who are survivors) and am generally not one to give men “benefit of the doubt” when I’m uninterested or uncomfortable.

The problem is, certain family members seem to consistently insinuate that I need to “fix” my dating life. I’ve made the mistake of mentioning that I eventually might be interested in marriage/kids, which has apparently given these family members permission to ask about why I’m not dating, give unsolicited advice about my dating life or lack thereof, and critique the way I interact with men. These family members did not approve of my previous relationship (and I understand why, although it’s truly none of their business) and seem to be motivated by a desire to see me “move on” from it. I always feel like they’re trying to tell me there’s something wrong with me for not being all that interested in dating; I’m also a pretty private person and don’t tend to talk about people I casually date/am interested in.

I’m at an age where a lot of my friends are in serious relationships and some are married, and the pressure is starting to get to me. Eventually, a relationship would be nice. I love kids and would like to have some of my own someday. But I need to do it on my own timeline, when I’m comfortable, when I figure out what I want and what I need. I’m not even 100% sure that I’m not bisexual. Scripts like “I don’t want to talk about my dating life/relationships” have only been interpreted as an invitation to “push” harder from these family members, and this lack of respect for my boundaries seems to be fraying my familial relationships that are really important to me. I want to be close with my family but I’m also an adult and need people to mind their own business, and I don’t know what to do. Any advice?

I’m a 20-year-old college student and I don’t drink, nor will I likely ever drink in the future. My father is an alcoholic, and every family member on his side has some form of substance abuse problem. I know that having a drink now and again will not necessarily hurt me or lead to a drinking problem of my own, but I’ve decided to just abstain completely anyways.

Most of my peers/classmates, however, like to drink and will often talk at length about it. I’ve been asked multiple times about my beer preference or some other alcohol-related question, to which I simply reply I don’t drink. For some reason, most people can’t seem to accept this and will ask me why not, or even try to convince me how great drinking is if I say it’s because I’m not interested. I don’t have a problem with other people drinking or listening to stories about it, but I don’t know how to explain my “disinterest” to other people.

I really don’t want to be a huge bummer in front of other people and say outright, “I don’t drink because my dad is an alcoholic,” but I don’t know how to get people to stop asking questions. “I don’t drink for personal reasons,” also feels like either a bummer or might lead to people asking what those reasons are.

So, Captain is there any way I can sidestep these questions without having to divulge my personal circumstances or bringing down the mood of the group?

I’m a 23 year old college student, and the kind of degree and profession I want to work in requires constant joint projects where working alone is not an option, and because our industry is so small, making good connections in college with your peers can be really important.

My problem is this: last semester, while working on a project together, a class mate told me he liked me and wanted to go out with me, and I turned him down because I wasn’t interested. We finished the project, he was professional, and I pulled back from hanging out at school because I didn’t want him to feel awkward.

Then the semester was over, we didn’t really talk, and when a new semester started, we hang out a bit more at school (sitting in class together, chatting at breaks), because I liked him as a friend and would have liked to work on more projects together. Two weeks ago we made some vague plans to go see a movie, he saw it without me so I offered to go to a different movie. We ate something and saw the movie (each of us paid for ourselves), and apparently he thought it was a date. Thing is, I deliberately leaned away from him and put my beg between us to not give the wrong impression. He took my bag and put it on the floor (wtf), then put his hand on my knee. He asked me if it was okay, I said no and he took his hand off. We’re on break from school now, and haven’t talked since.

I’m mad at him, and I don’t know if I’m being cruel or not. On one hand I’m pissed off he just assumed I changed my mind. On the other hand, did he harbored a crush on me for months and I was careless with his feelings? Did I sent the wrong signals, or did he ignored the signals I sent? Should I assume he is not interested in being friends?

Truth is, I’m a very traditionally attractive woman and I usually gets more romantic\sexual attention than I would like. I work with other women on projects, but only working with ladies will really limit my options.The whole not-date throw me into a spiral of insecurities (I’m not really talented, nobody really likes me, guys lie to me and only put up with me because I’m pretty etc) and I’m feeling really shitty right now, and I can’t focus on my school work. What can I do to make things better, and to prevent situations like this in the future?

I love your site and have read 99% of your archive. I love the honesty and practicality of your responses and find a lot of helpful truth in them. This one, though, is stymieing me.

I have built a career that has been very successful and train people in complex aspects of my profession.

Since there are multiple cycles of the sessions required for industry certification, I get a lot of the same participants over and over, and one such is the worst energy vampire I’ve met in my entire life. I’m running out of ways to deal with her short of telling my boss to cut her out completely, thus hurting her career pretty permanently. I work hard to be patient, professional, and kind to everyone, but this woman, Emma, is beyond my capabilities.

Emma lives alone, and her husband either died under tragic and improbable circumstances or left her under equally tragic and improbable circumstances or there never was a husband at all; she was apparently adopted by a cruel aunt as a child, but that story has shifted as well and sounds suspiciously like Harriet Potter or at least A Little Princess. Each session now drags on as she rambles, and regardless of what we are discussing (usually content-specific and related to our set purpose) she finds an entry point to share irrelevant anecdotes incoherently and at length. With no exception, the other participants in each session despise this woman, and come to me privately to “deal with her.” She has been questioned on inconsistencies in her narrative by members of the group only to rail at how unfair everyone is to her and WHY WILL NO ONE BELIEVE THAT MY LIFE IS HARDER THAN YOURS. She never submits her assignments, and thus takes the sessions again and again and again (paying full price each time, so my boss just shrugs and takes her money) but the behavior never changes and it’s The Emma Show.

She has my office number due to its placement on my syllabi, but not my cell, although she asks me for it every single meeting so we “can socialize” because “you’re my sister from another mother!” She desperately wants to be friends on social media, and I have firmly told her I don’t do that with work acquaintances. She wants us to get matching tattoos. I have said no with increasing hostility to each of these overtures and repeatedly said, “Emma, I understand that you would like us to be friends, but I have to maintain professional boundaries and I know you’ll understand that I can’t breach those roles,” to which she will inevitably sigh, giggle, and pet my arm while saying, “Soon! I’ll graduate from the cycle and we can HANG OUT!”

Okay. I know that this woman is desperately lonely and probably struggles with the truth (even to herself), and I SHOULD be sympathetic. I have asked my boss to schedule her with another instructor, but my boss doesn’t want Emma in her own sessions again so I’m it. It’s to the point now that I don’t honestly know what to do short of open warfare.

Practical suggestions? A script? If I remove her from my roster it will have immediate and negative repercussions on her full-time employment and I don’t know if I can ethically do that to someone who, let’s face it, I just dislike. I strive to be a good person but my God she is testing this each time.

I hate how she eats French fries. (EVERY SESSION. LOUDLY. WITH MAYONNAISE WHO DOES THAT.)

I hate how she pronounces “nuc-u-ler.”

I hate how she monopolizes everyone’s time, in small groups, or pairs, or whole-group activities, no matter what I do, say, relocate, or attempt. (And yes, I know how to deal with teenagers with oppositional behaviors, just not forty-year-olds who insist they are grownups.) I move her seat; she cries and moves back. I tell her I can’t pass her due to lack of work; she blames her seat mate. I tell her not to talk tonight because other people need to share and work through their (work-related) issues; she interrupts and says her problems are more important. I feel impotent because my boss will NOT back me up.

(And I hate, hate, hate going to the bathroom after her, but that’s another story for never.)

I recently finalized the ending of a relationship…I say finalized because I’ve been trying to break up with my ex since October, but she finally was able to accept it months later…no matter how many times I told her, “my feelings for you have changed,” “I’m no longer attracted to you,” et al. For the record, she’s not a bad person…hardcore GSF carrier, yes, but a generally decent, well intentioned (if a little misguided a lot of the time) human being. When the ending finally hit her, we were able to talk more openly than we have in months and are working out all the transitional stuff without conflict.

The question is this…we rent an apartment together with me taking on the bulk of the expenses as I make more money. While I could likely move with ease, she’s not in the same position…she wants us to stay as platonic roommates for another year, continue to work on our friendship as we move forward with our separate lives. Most of my Team Me think I am nuts for considering it. I’m torn. I don’t want to be the person who says, “F You, I don’t care, I am looking out for me,” but I want to be sure that I – and she, for that matter – can move on with our lives and be okay with it. I’m at the point where if I saw her with someone else, I’d be totally happy for her. No jealously, no angst. I don’t know that I trust her to be okay in the same way. It worries me that she refused to hear the very explicit statements I was making with regard to wanting to end our relationship, and I worry about how that could pan out should I meet someone else. On the other, we do work together in terms of splitting things up around the house well, and have pretty much been platonic roommates for the last year of our relationship.

Is this worth it to save money and hassle, or should I run, run, run?

Thanks, Domestically Challenged

Dear Domestically Challenged,

Listen to your friends!

RUN!

EXCLAMATION POINTS! YELLING!

You have been trying to break up with this person, by my count, FOR FIVE MONTHS. I just met you (sort of) but your friends have been watching this saga unfold and if they say “Run!” I say “Run!”

Breaking up is a unilateral decision. When you say, “My feelings have changed and I am breaking up with you” the relationship is over! The other person does not have to agree or consent for this to be true. And once you break up, one of the pieces of good news is that you get to stop “working on” the relationship. Some exes make great friends, and sometimes the transition is pretty easy because face it, you already were more like friends and like lovers. Not so with someone who refuses to accept the reality of your breakup and thinks you should “work on” that for another YEAR of your life.

Have you ever heard the expression “Sometimes the cheapest way to pay is with money?” I think it’s a nice gesture for the ex who makes more money to help the person who has less in the event of a breakup and dissolution of households, and if you can afford to pull together a security deposit-ish fund you could give her, it would be a kind gesture. On the one hand, your ex has manipulated you into staying longer than you want to and she has had five months to ponder “Domestically Challenged seems to be making noises about ending our relationship, so where would I live if we were to break up and not live together anymore?” and you don’t owe her any money (or more time). In your shoes, I would prioritize getting yourself out first and helping her second, if at all. On the other hand, sometimes the cheapest way to pay is with money.

Before you contemplate continuing a friendship with your ex, I think you need a space of your own away from her where you can hear yourself think, not another year (!!!!!) of dragging this out. Tell her you don’t want to keep living together. Offer her some relocation money if that’s something you can do. Consider staying with a friend for a few days to give her time to process the decision. Then move out of FEELINGSHAUS and into the next phase of your life. Then figure in where (and if) your ex fits into your life as a friend.

My mom has always been on about how I look, but since I’ve turned 16 it seems to have gotten worse. She got me a fitbit that she makes me use (which I hate because it tells me I eat too many calories a day, even though it’s the recommended amount), made me diet with her, and constantly makes comments on how “I should go to the gym more,” even though I’m a perfectly healthy weight for my height. If i’m about to leave the house with no makeup on, she says “Oh why don’t you put a little foundation and mascara on before you go?” and is visibly embarrassed if she sees m in public wit none on. She also hates me wearing my glasses, as they “cover up my beautiful face” and will make more comments on them if I wear them outside the house instead of my contacts. My boobs aren’t very big, but my thighs are, so she’s always pushing me to wear push up bras and slimming clothes. It’s gotten to the point where I’m embarrassed to not be made up, am starting to obsess over my weight, and am just downright lacking in self-esteem. I’ve tried bringing it up before, but she either plays the victim or pretends like she never did any of that. Any advice on what I can do?